Jack Raines liked his boss on Hinge.
It wasn’t reciprocal. A few months later, three beers deep at a bar, he told her he was quitting — then found a $250 plane ticket to Barcelona and left the country […]
Category: Personal Finance 101
#738: Hackers Waited 3 Months for This Couple’s $1.2 Million Deal, with Dr. Eric Cole [GREATEST HITS]
Hackers broke into a real estate closing company’s servers and waited three months for the right deal — then intercepted a wire and stole $1.2 million from a couple who did everything right, right down to the closing table.
Dr. Eric Cole was a former […]
#728: Q&A: What $2.4 Million at 37 Actually Looks Like (It’s Not What You Think)
What happens when a sudden $850,000 inheritance turns into eight different account balances, three rental properties, and one very big decision about your future?
When grief, real estate, and a six-figure windfall collide all at once, the fastest way to make an expensive mistake is to rush […]
#725: What Most Families Get Wrong About Passing Down Wealth, with Andrea Baumann Lustig
When it comes to our money, the things we feel most certain about are often the exact blind spots that quietly derail our long-term plans.
We hold onto financial beliefs as if they’re religion or politics, rarely checking if they actually serve our long-term legacy goals.
Veteran […]
#723: Six Levels of Wealth, with Nick Maggiulli [Greatest Hits]
It turns out that almost everything we’re taught about personal finance is completely backward if you try to use the same advice your entire life.
What works perfectly when you have $10,000 in the bank will completely stall you out once you hit $1 million.
Yet most money advice treats […]
#722: Q&A: Why Do I Still Feel Anxious When I’m Clearly Doing Well?
Ever feel like your money plan looks perfect on paper, but you’re still stressed out about it?
While spreadsheets give us the exact math, how we feel about our wealth is a whole different story.
Joe and I dive into the big gap between money logic and human psychology to help you […]
#718: Q&A: The Goalposts Moved — Is That Actually a Problem?
As we edge closer to financial independence, a funny thing happens to the finish line: it often starts to move.
But the goalposts don’t always shift because of lifestyle inflation or uncontrolled spending.
Sometimes, they move because our vision for our wealth expands—particularly when it comes to long-term charitable giving, family legacy, […]
#717: The 5 Ways Investors Behave When Things Go Wrong, with Clare Flynn Levy
When a crisis hits the stock market, we tend to think that data, algorithms, and cold logic rule the day.
But behind every major investment portfolio is a human being subject to the exact same psychological traps, behavioral blind spots, and emotional relationships that affect everyday investors.
We sit down with Clare […]
#716: Q&A: Your Kids Just Inherited $350,000 Each. Now What
We are currently on the precipice of the largest transfer of wealth in human history.
Over the next two decades, an estimated $84 trillion to $100 trillion will pass from older generations to younger ones.
This shift will fundamentally change the economic landscape, but for the individuals involved, it often starts with […]
#715: Mrs. Dow Jones: Your Childhood Is Running Your Bank Account
She grew up with a Goldman Sachs dad. She still ended up broke in her 20’s.
Haley Sacks—known online as Mrs. Dow Jones—joins us to talk about the five-step financial framework she calls IBIZA.
Despite every advantage, she spent her twenties anxious, financially dependent, and charging dinners to her parents’ […]
